US6359069B1 - Transparent composition containing polycarbonate and a copolymer of methylmethacrylate - Google Patents

Transparent composition containing polycarbonate and a copolymer of methylmethacrylate Download PDF

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Publication number
US6359069B1
US6359069B1 US09/636,200 US63620000A US6359069B1 US 6359069 B1 US6359069 B1 US 6359069B1 US 63620000 A US63620000 A US 63620000A US 6359069 B1 US6359069 B1 US 6359069B1
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United States
Prior art keywords
copolymer
polycarbonate
hydroxyphenyl
bis
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
US09/636,200
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English (en)
Inventor
Pierre Moulinié
Nicanor Köhncke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Corp
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Bayer Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Corp filed Critical Bayer Corp
Assigned to BAYER CORPORATION reassignment BAYER CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KOHNCKE, NICANOR, MOULINIE, PIERRE
Priority to US09/636,200 priority Critical patent/US6359069B1/en
Priority to JP2002519559A priority patent/JP2004506771A/ja
Priority to DE60118394T priority patent/DE60118394T2/de
Priority to ES01959541T priority patent/ES2260263T3/es
Priority to EP01959541A priority patent/EP1313806B1/en
Priority to CNB018171567A priority patent/CN1203127C/zh
Priority to AT01959541T priority patent/ATE321817T1/de
Priority to BR0113063-3A priority patent/BR0113063A/pt
Priority to KR10-2003-7001873A priority patent/KR20030026337A/ko
Priority to PCT/US2001/024549 priority patent/WO2002014427A2/en
Priority to HK04105262.6A priority patent/HK1062309B/xx
Publication of US6359069B1 publication Critical patent/US6359069B1/en
Application granted granted Critical
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/10—Homopolymers or copolymers of methacrylic acid esters
    • C08L33/12—Homopolymers or copolymers of methyl methacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates

Definitions

  • the present invention is directed to a thermoplastic molding composition and more particularly to a transparent blend that contains polycarbonate resin and atactic copolymer of PMMA.
  • thermoplastic molding composition containing polycarbonate resin and a copolymer of methyl methacrylate conforming structurally to:
  • x and y are integers calculated to result in a content of PMMA in the copolymer in the range of 80 to 90 mole %, and wherein x and y are integers calculated to result in a content of PMMA in the copolymer in the range of 80 to 90 mole %, and where R 1 denotes —CH 3 , R 2 denotes —C 6 H 5 and R 3 is a C 1 -C 2 -alkyl group.
  • composition is useful in preparing transparent articles, including films.
  • Polycarbonate resins are characterized by dimensional stability at relatively high temperatures, excellent resistance to impact, stiffness and transparency. These properties make polycarbonate the material of choice for a variety of applications including glazing containers and medical devices.
  • a notable drawback characterizing this resin has been its susceptibility to scratching.
  • Polymethylmethacrylate (“PMMA”) known for its clarity and scratch resistance is noted for its shortcomings in terms of dimensional stability, low impact strength and relatively poor thermal stability. While some blends of polycarbonates and PMMA reflecting a more attractive profile of properties are known, it is also known that a wide range of blends with typical PMMA are immiscible and opaque. It has been suggested that free radical polymerized PMMA does not form a single thermo-dynamically miscible transparent blend but does demonstrate mechanical compatibility with polycarbonate. While this compatibility is taken to mean that the phases exhibit good adhesion one to the other, the resulting blend is not transparent.
  • Literature relative to mixtures of polycarbonate and PMMA include U.S. Pat. No. 4,319,003 that disclosed opaque blends. Also noted in this connection are JP 7216063 and EP 297285. Ways of overcoming the drawbacks associated with the immiscibility of PMMA and polycarbonate have been proposed. These include the addition of copolymer additives (DE 2264268); PMMA/acrylamide copolymers (DE 3632946 and PMMA-ester copolymers containing carboxylic groups (U.S. Pat. No. 4,906,696). Further, transparent blends of PMMA and polycarbonate are said to have been prepared, in accordance with DE 3,833,218, by melting the two components in the presence of supercritical gas. U.S. Pat.
  • the present invention concerns a thermoplastic molding composition containing polycarbonate and a specifically structured copolymer of methyl methacrylate (herein “COPMA”).
  • COPMA methyl methacrylate
  • the composition containing about 5 to 20, preferably 7 to 15 percent of a suitable COPMA, the percent being relative to the total weight of polycarbonate and COPMA is characterized by its transparency.
  • the inventive transparent blend may be processed thermoplastically in accordance with conventional procedures and using conventional means.
  • Aromatic polycarbonates within the scope of the present invention are homopolycarbonates, copolycarbonates, branched polycarbonates and mixtures thereof.
  • the polycarbonates generally have a weight average molecular weight of 10,000 to 200,000, preferably 20,000 to 80,000 and their melt flow rate, per ASTM D-1238 at 300° C., is about 1 to about 65 g/10 min., preferably about 2 to 15 g/10 min.
  • They may be prepared, for example, by the known diphasic interface process from a carbonic acid derivative such as phosgene and dihydroxy compounds by polycondensation (see German Offenlegungsschriften 2,063,050; 2,063,052; 1,570,703; 2,211,956; 2,211,957 and 2,248,817; French Patent 1,561,518; and the monograph H. Schnell, “Chemistry and Physics of Polycarbonates”, Interscience Publishers, New York, N.Y., 1964 (all incorporated herein by reference).
  • a carbonic acid derivative such as phosgene and dihydroxy compounds by polycondensation
  • dihydroxy compounds suitable for the preparation of the polycarbonates of the invention conform to the structural formulae (1) or (2):
  • A denotes an alkylene group with 1 to 8 carbon atoms, an alkylidene group with 2 to 8 carbon atoms, a cycloalkylene group with 5 to 15 carbon atoms, a cycloalkylidene group with 5 to 15 carbon atoms, a carbonyl group, an oxygen atom, a sulfur atom, —SO— or —SO 2 — or a radical conforming to:
  • e and g both denote the number 0 to 1;
  • Z denotes F, Cl, Br or C 1 -C 4 -alkyl and if several Z radicals are substituents in one aryl radical, they may be identical or different from one another;
  • d denotes an integer of from 0 to 4; and
  • f denotes an integer of from 0 to 3.
  • dihydroxy compounds useful in the practice of the invention are hydroquinone, resorcinol, bis-(hydroxyphenyl)-alkanes, bis-(hydroxyphenyl)-ethers, bis-(hydroxyphenyl)-ketones, bis-(hydroxyphenyl)-sulfoxides, bis-(hydroxyphenyl)-sulfides, bis-(hydroxyphenyl)-sulfones, and ⁇ , ⁇ -bis-(hydroxyphenyl)-diisopropylbenzenes, as well as their nuclearalkylated compounds.
  • aromatic dihydroxy compounds are described, for example, in U.S. Pat. Nos. 3,028,356; 2,999,835; 3,148,172; 2,991,273; 3,271,367; and 2,999,846, all incorporated herein by reference.
  • suitable bisphenols are 2,2-bis-(4-hydroxyphenyl)-propane (bisphenol A), 2,4-bis-(4-hydroxyphenyl)-2-methylbutane, 1,1-bis-(4-hydroxyphenyl)-cyclohexane, ⁇ , ⁇ ′-bis-(4-hydroxyphenyl)-p-diisopropylbenzene, 2,2-bis-(3-methyl-4-hydroxyphenyl)-propane, 2,2-bis-(3-chloro4-hydroxyphenyl)-propane, bis-(3,5-dimethyl4-hydroxyphenyl)-methane, 2,2-bis-(3,5-dimethyl-4-hydroxyphenyl)-propane, bis-(3,5-dimethyl-4-hydroxyphenyl)-sulfide, bis-(3,5-dimethyl-4-hydroxyphenyl)-sulfoxide, bis-(3,5-dimethyl-4-hydroxyphenyl)-sulfone, dihydroxybenz
  • aromatic bisphenols examples include 2,2,-bis-(4-hydroxyphenyl)-propane, 2,2-bis-(3,5-dimethyl-4-hydroxyphenyl)-propane, 2,2,4-trimethyl cyclohexyl 1,1-diphenol and 1,1-bis-(4-hydroxyphenyl)-cyclohexane.
  • bisphenol A 2,2-bis-(4-hydroxyphenyl)-propane
  • the polycarbonates of the invention may entail in their structure units derived from one or more of the suitable bisphenols.
  • COPMA copolymer of methyl methacrylate of the present invention
  • R 1 denotes —CH 3
  • R 2 denotes —C 6 H 5
  • R 3 is hydrogen or a C 1 -C 2 -alkyl group.
  • the preparation of the inventive COPMA may be carried out by free radical polymerization of methyl methacrylate in the presence of an appropriate vinyl-benzoate comonomer.
  • Suitable benzoate monomer may be synthesized from ⁇ -methyl-para-hydroxystyrene with benzoyl chloride in the presence of an amine base (such as triethylamine).
  • an amine base such as triethylamine
  • Blends in accordance with the invention were prepared and their properties were determined.
  • the polycarbonate component of all the exemplified blends was a homopolycarbonate based on bisphenol A (Makrolon 2608, a product of Bayer Corporation).
  • a low shear melt kneader was used, operating at 280° C. for 20 to 25 minutes.
  • Additional inventive blends were prepared in a 16 mm twin-screw extruder which has conveying and mixing sections along the extruder screws at 250 to 285° C. No catalysts or other additives are necessary for preparing the transparent materials.
  • the blends contained 90 wt. % polycarbonate and 10 wt % COPMA (the COPMA containing 90 mole % MMA). These were injection molded conventionally to make test specimens for determination of optical properties (see results below in Table 2).
  • a comparative example containing 90 wt % polycarbonate and 10 wt % PMMA were prepared by the same procedures and optical properties (total light transmission —TLT— and haze) of specimens thus molded were determined (in accordance with ASTM D 1003). These are reported below (see Table 2).
  • composition in accordance with the invention exhibit far better optical properties than does a corresponding, largely similar composition.
  • MMA denotes units derived from methylmethacrylate comonomer
  • copolymer of the invention —COPMA conforming to:

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US09/636,200 2000-08-10 2000-08-10 Transparent composition containing polycarbonate and a copolymer of methylmethacrylate Expired - Fee Related US6359069B1 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
US09/636,200 US6359069B1 (en) 2000-08-10 2000-08-10 Transparent composition containing polycarbonate and a copolymer of methylmethacrylate
AT01959541T ATE321817T1 (de) 2000-08-10 2001-08-02 Transparente zusammensetzung enthaltend ein polycarbonat und ein methylmethacrylat-copolymer
KR10-2003-7001873A KR20030026337A (ko) 2000-08-10 2001-08-02 폴리카르보네이트 및 메틸메타크릴레이트의 공중합체를포함하는 투명 조성물
ES01959541T ES2260263T3 (es) 2000-08-10 2001-08-02 Composicion transparente que contiene policarbonato y un copolimero demetacrilato de metilo.
EP01959541A EP1313806B1 (en) 2000-08-10 2001-08-02 A transparent composition containing polycarbonate and a copolymer of methylmethacrylate
CNB018171567A CN1203127C (zh) 2000-08-10 2001-08-02 含聚碳酸酯及甲基丙烯酸甲酯的共聚物的透明组合物
JP2002519559A JP2004506771A (ja) 2000-08-10 2001-08-02 ポリカーボネートおよびメチルメタクリレートコポリマーを含有する透明な熱可塑性成形用組成物
BR0113063-3A BR0113063A (pt) 2000-08-10 2001-08-02 Composição transparente contendo policarbonato e um copolìmero de metilmetacrilato
DE60118394T DE60118394T2 (de) 2000-08-10 2001-08-02 Transparente Zusammensetzung enthaltend ein Polycarbonat und ein Methylmethacrylat-Copolymer
PCT/US2001/024549 WO2002014427A2 (en) 2000-08-10 2001-08-02 A transparent composition containing polycarbonate and a copolymer of methylmethacrylate
HK04105262.6A HK1062309B (en) 2000-08-10 2001-08-02 A transparent composition containing polycarbonate and a copolymer of methylmethacrylate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US09/636,200 US6359069B1 (en) 2000-08-10 2000-08-10 Transparent composition containing polycarbonate and a copolymer of methylmethacrylate

Publications (1)

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US6359069B1 true US6359069B1 (en) 2002-03-19

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Country Status (10)

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US (1) US6359069B1 (enExample)
EP (1) EP1313806B1 (enExample)
JP (1) JP2004506771A (enExample)
KR (1) KR20030026337A (enExample)
CN (1) CN1203127C (enExample)
AT (1) ATE321817T1 (enExample)
BR (1) BR0113063A (enExample)
DE (1) DE60118394T2 (enExample)
ES (1) ES2260263T3 (enExample)
WO (1) WO2002014427A2 (enExample)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080241749A1 (en) * 2007-03-30 2008-10-02 Fujifilm Corporation Positive resist composition and pattern forming method using the same
US20080241743A1 (en) * 2007-03-27 2008-10-02 Fujifilm Corporation Positive resist composition and pattern forming method using the same
JP2012167195A (ja) * 2011-02-15 2012-09-06 Sumitomo Chemical Co Ltd 樹脂組成物の製造方法、樹脂組成物及び成形体
US8691915B2 (en) 2012-04-23 2014-04-08 Sabic Innovative Plastics Ip B.V. Copolymers and polymer blends having improved refractive indices
JP2015208961A (ja) * 2014-04-28 2015-11-24 住友ベークライト株式会社 多層樹脂シート、液晶保護シート、建築基材用窓材、産業機械用窓材、または商品陳列什器用窓材。
US10731033B2 (en) 2013-10-07 2020-08-04 Mitsubishi Gas Chemical Company, Inc. (Meth)acrylic copolymer, resin composition, and molded product of said resin composition

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10351535A1 (de) 2003-11-03 2005-06-09 Röhm GmbH & Co. KG Mehrschichtfolie aus (Meth)acrylatcopolymer und Polycarbonat
WO2019029794A1 (en) * 2017-08-09 2019-02-14 Transitions Optical, Ltd. CURABLE PHOTOCHROMIC COMPOSITION COMPRISING A SEGMENTED POLYMER
CN113388219B (zh) * 2021-06-30 2022-12-27 新纶新材料股份有限公司 一种光学薄膜材料、柔性防爆膜及其制备方法、电子设备

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1394481A (en) 1972-01-03 1975-05-14 Gen Electric Polycarbonate moulding composition
US4319003A (en) 1980-09-26 1982-03-09 General Motors Corporation Poly(methyl methacrylate) polycarbonate block copolymers
US4743654A (en) 1986-11-13 1988-05-10 University Of Akron Single phase blends of polycarbonate and polymethyl methacrylate
US4745029A (en) 1986-10-06 1988-05-17 General Electric Company Transparent blends of polymethyl methacrylate and BPA polycarbonate
US4749749A (en) 1986-09-27 1988-06-07 Rohm Gmbh Chemische Fabrik Compatible mixtures of a polycarbonate and a methacrylate copolymer
US4906696A (en) 1987-06-06 1990-03-06 Rohm Gmbh Chemische Fabrik Transparent, thermoplastically processable polymer blends made of an aromatic polycarbonate and a methyacrylate polymer
DE3833218A1 (de) 1988-09-30 1990-04-05 Bayer Ag Verfahren zur herstellung von transparenten mischungen aus aromatischen polycarbonaten und poly-c(pfeil abwaerts)1(pfeil abwaerts)-c(pfeil abwaerts)8(pfeil abwaerts)-alkyl-(meth)acrylaten
EP0573109A2 (en) 1992-06-01 1993-12-08 ENICHEM S.p.A. Polycarbonate-polymethyl methacrylate blends
US5284916A (en) 1992-09-30 1994-02-08 Istituto Guido Donegani S.P.A. Block copolymers containing polyaromatic(alkyl)methacrylates and their blends with polycarbonates
JPH07216063A (ja) 1994-01-28 1995-08-15 Mitsui Toatsu Chem Inc ポリヒドロキシカルボン酸の製造方法
US6111133A (en) * 1992-09-23 2000-08-29 Lucent Technologies Inc. Process for preparing substituted styrenes

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1394481A (en) 1972-01-03 1975-05-14 Gen Electric Polycarbonate moulding composition
US4319003A (en) 1980-09-26 1982-03-09 General Motors Corporation Poly(methyl methacrylate) polycarbonate block copolymers
US4749749A (en) 1986-09-27 1988-06-07 Rohm Gmbh Chemische Fabrik Compatible mixtures of a polycarbonate and a methacrylate copolymer
US4745029A (en) 1986-10-06 1988-05-17 General Electric Company Transparent blends of polymethyl methacrylate and BPA polycarbonate
US4743654A (en) 1986-11-13 1988-05-10 University Of Akron Single phase blends of polycarbonate and polymethyl methacrylate
US4906696A (en) 1987-06-06 1990-03-06 Rohm Gmbh Chemische Fabrik Transparent, thermoplastically processable polymer blends made of an aromatic polycarbonate and a methyacrylate polymer
DE3833218A1 (de) 1988-09-30 1990-04-05 Bayer Ag Verfahren zur herstellung von transparenten mischungen aus aromatischen polycarbonaten und poly-c(pfeil abwaerts)1(pfeil abwaerts)-c(pfeil abwaerts)8(pfeil abwaerts)-alkyl-(meth)acrylaten
EP0573109A2 (en) 1992-06-01 1993-12-08 ENICHEM S.p.A. Polycarbonate-polymethyl methacrylate blends
US6111133A (en) * 1992-09-23 2000-08-29 Lucent Technologies Inc. Process for preparing substituted styrenes
US5284916A (en) 1992-09-30 1994-02-08 Istituto Guido Donegani S.P.A. Block copolymers containing polyaromatic(alkyl)methacrylates and their blends with polycarbonates
JPH07216063A (ja) 1994-01-28 1995-08-15 Mitsui Toatsu Chem Inc ポリヒドロキシカルボン酸の製造方法

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080241743A1 (en) * 2007-03-27 2008-10-02 Fujifilm Corporation Positive resist composition and pattern forming method using the same
US7592118B2 (en) * 2007-03-27 2009-09-22 Fujifilm Corporation Positive resist composition and pattern forming method using the same
US20080241749A1 (en) * 2007-03-30 2008-10-02 Fujifilm Corporation Positive resist composition and pattern forming method using the same
JP2012167195A (ja) * 2011-02-15 2012-09-06 Sumitomo Chemical Co Ltd 樹脂組成物の製造方法、樹脂組成物及び成形体
US8691915B2 (en) 2012-04-23 2014-04-08 Sabic Innovative Plastics Ip B.V. Copolymers and polymer blends having improved refractive indices
US10731033B2 (en) 2013-10-07 2020-08-04 Mitsubishi Gas Chemical Company, Inc. (Meth)acrylic copolymer, resin composition, and molded product of said resin composition
JP2015208961A (ja) * 2014-04-28 2015-11-24 住友ベークライト株式会社 多層樹脂シート、液晶保護シート、建築基材用窓材、産業機械用窓材、または商品陳列什器用窓材。

Also Published As

Publication number Publication date
WO2002014427A8 (en) 2003-08-21
HK1062309A1 (en) 2004-10-29
EP1313806A2 (en) 2003-05-28
ATE321817T1 (de) 2006-04-15
DE60118394T2 (de) 2006-11-02
JP2004506771A (ja) 2004-03-04
ES2260263T3 (es) 2006-11-01
KR20030026337A (ko) 2003-03-31
BR0113063A (pt) 2003-07-08
WO2002014427A3 (en) 2002-08-01
CN1469904A (zh) 2004-01-21
EP1313806B1 (en) 2006-03-29
WO2002014427A2 (en) 2002-02-21
DE60118394D1 (de) 2006-05-18
CN1203127C (zh) 2005-05-25

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